In this article we critically examine the principle of equivalence of care in prison medicine. First, we provide an overview of how the principle of equivalence is utilized in various national and international guidelines on health care provision to prisoners. Second, we outline some of the problems associated with its applications, and argue that the principle of equivalence should go beyond equivalence to access and include equivalence of outcomes. However, because of the particular context of the prison environment, third, we contend that the concept of “health” in equivalence of health outcomes needs conceptual clarity; otherwise, it fails to provide a threshold for healthy states among inmates. We accomplish this by examining common understandings of the concepts of health and disease. We conclude our article by showing why the conceptualization of diseases as clinical problems provides a helpful approach in the delivery of health care in prison.